2-benzyl-1-methyl-4-(3-methylene-3l5-buta-1,3-dien-1-yl)benzene | 1266754-18-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzyl-1-methyl-4-(3-methylene-3l5-buta-1,3-dien-1-yl)benzene
• CAS: 1266754-18-0
• 化学式: C₁₄H₁₀FNO₃
• 分子量: 259.237
• InChiKey: ZJBILOWACNVSGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-benzyl-1-methyl-4-(3-methylene-3l5-buta-1,3-dien-1-yl)benzene 、 3-Oxo-3--propionsaeureaethylester 在 (8Α,9R)-9-(9-苯基甲氧基)奎宁-6'-醇 、 四甲基胍 作用下， 以 二氯甲烷 为溶剂， 反应 40.5h， 生成 ethyl 6-(4-fluoro-3-phenoxyphenyl)-4-hydroxy-7-nitro-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carboxylate
  参考文献：
  名称：

  Organocatalytic Sequential Michael Reactions: Stereoselective Synthesis of Multifunctionalized Tetrahydroindan Derivatives

  摘要：

  Multifunctionalized tetrahydroindan derivatives with four stereocenters were constructed via two sequential Michael reactions between cyclic gamma,delta-unsaturated-beta-ketoester and nitroalkenes initiated with 0.5-2 mol % of cinchona alkaloid based bifunctional organocatalysts and then with 1 equiv of tetramethylguanidine for cyclization. The desired products could be obtained in high yields (up to 99% yield) with excellent enantioselectivities (95-99% ee) as well as diastereoselectivities (up to >99:1 dr) even on a gram scale.

  DOI：

  10.1021/ol1029832

文献信息

• Bifunctional Guanidine via an Amino Amide Skeleton for Asymmetric Michael Reactions of β-Ketoesters with Nitroolefins: A Concise Synthesis of Bicyclic β-Amino Acids
  作者：Zhipeng Yu、Xiaohua Liu、Lin Zhou、Lili Lin、Xiaoming Feng

  DOI：10.1002/anie.200901337

  日期：2009.6.29

  Two activations are better than one: The chiral bifunctional guanidine 1, which features an amino amide backbone, catalyzes the asymmetric Michael addition of a range of substrates and gives products with excellent stereoselectivities. The method also allows the efficient synthesis of optically pure β‐amino acid esters. Both the guanidine group and the NH proton of the amide were important for the

  两种活化优于一种：氨基氨基骨架的手性双官能胍1催化一系列底物的不对称迈克尔加成反应，并提供具有出色立体选择性的产物。该方法还可以有效合成光学纯的β-氨基酸酯。胍基和酰胺的NH质子均对双重活化很重要。